(5Z)-3-(2-Oxoprop­yl)-5-(3,4,5-tri­meth­oxy­benzyl­idene)-1,3-thia­zol­idine-2,4-dione

In the crystal of the title mol­ecule, C₁₆H₁₇NO₆S, there are three sets of inter­molecular C—H...O hydrogen bonds, as well as two sets of inter­molecular C—H...π(ring) inter­actions. In addition, the thia­zol­idene rings participate in offset π–π stacking inter­actions [centroid–centroid distance = 3.685 (1) Å]. These generate small channels running parallel to the a axis with approximate cross-sections of 3.7 × 8.1 Å.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.111
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.22 Report
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     --  C13     ..        5.2 s.u.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2 Report

Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         93 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(5Z)-3-(2-Oxopropyl)-5-(3,4,5-trimethoxybenzylidene)-1,3-thiazolidine-2,4-dione

Crystal data

C16H17NO6S	Z = 2
Mr = 351.36	F(000) = 368
Triclinic, P1	Dx = 1.471 Mg m^−3
a = 7.2771 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9612 (7) Å	Cell parameters from 9211 reflections
c = 11.9257 (8) Å	θ = 2.6–29.3°
α = 78.778 (1)°	µ = 0.24 mm^−1
β = 75.616 (1)°	T = 100 K
γ = 72.829 (1)°	Block, colourless
V = 793.16 (9) Å^3	0.33 × 0.22 × 0.21 mm

Data collection

Bruker SMART APEX CCD diffractometer	4235 independent reflections
Radiation source: fine-focus sealed tube	3660 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.3333 pixels mm^-1	θmax = 29.3°, θmin = 1.8°
φ and ω scans	h = −10→9
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −13→13
Tmin = 0.88, Tmax = 0.95	l = −16→16
15337 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: difference Fourier map
wR(F^2) = 0.111	All H-atom parameters refined
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0762P)^2 + 0.0197P] where P = (Fo^2 + 2Fc^2)/3
4235 reflections	(Δ/σ)max < 0.001
285 parameters	Δρmax = 0.53 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3

Special details

Experimental. The diffraction data were obtained from 3 sets of 400 frames,

each of width 0.5° in ω, colllected at φ = 0.00,

90.00 and 180.00° and 2 sets of 800 frames, each of

width 0.45° in φ, collected at ω = –30.00 and 210.00°.

The scan time was 15 sec/frame.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell esds are taken

into account individually in the estimation of esds in distances, angles

and torsion angles; correlations between esds in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F², conventional R-factors R are based

on F, with F set to zero for negative F². The threshold expression of

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F² are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.48040 (4)	0.43973 (3)	0.23681 (2)	0.01742 (10)
O1	0.03935 (12)	0.33614 (9)	0.63528 (7)	0.01876 (18)
O2	−0.28654 (12)	0.25762 (9)	0.64722 (7)	0.01887 (18)
O3	−0.33832 (11)	0.15463 (9)	0.46574 (7)	0.01978 (19)
O4	0.52749 (13)	0.21005 (10)	0.00080 (7)	0.0234 (2)
O5	0.80964 (14)	0.50044 (10)	0.11411 (8)	0.0261 (2)
O6	0.97444 (13)	0.12856 (9)	0.08413 (7)	0.02220 (19)
N1	0.68693 (13)	0.35869 (10)	0.03734 (8)	0.0158 (2)
C1	0.12221 (16)	0.26129 (12)	0.33290 (9)	0.0155 (2)
C2	0.15413 (16)	0.30468 (12)	0.42980 (9)	0.0161 (2)
H2	0.270 (2)	0.3321 (17)	0.4249 (14)	0.030 (4)*
C3	0.02037 (16)	0.29904 (11)	0.53540 (9)	0.0149 (2)
C4	−0.14759 (16)	0.25128 (11)	0.54493 (9)	0.0153 (2)
C5	−0.17503 (16)	0.20396 (12)	0.44871 (10)	0.0158 (2)
C6	−0.04092 (16)	0.20892 (12)	0.34351 (10)	0.0159 (2)
H6	−0.058 (2)	0.1776 (14)	0.2782 (13)	0.021 (4)*
C7	0.21364 (18)	0.38004 (13)	0.62923 (10)	0.0199 (2)
H7A	0.203 (2)	0.4033 (16)	0.7063 (13)	0.027 (4)*
H7B	0.328 (2)	0.2998 (15)	0.6124 (13)	0.022 (4)*
H7C	0.218 (2)	0.4641 (15)	0.5688 (13)	0.020 (3)*
C8	−0.2732 (2)	0.12561 (14)	0.72236 (11)	0.0234 (3)
H8A	−0.297 (2)	0.0581 (17)	0.6826 (14)	0.030 (4)*
H8B	−0.382 (2)	0.1412 (16)	0.7911 (14)	0.029 (4)*
H8C	−0.145 (3)	0.0923 (17)	0.7438 (14)	0.034 (4)*
C9	−0.33885 (18)	0.07211 (13)	0.38013 (11)	0.0201 (2)
H9A	−0.228 (2)	−0.0124 (15)	0.3783 (12)	0.022 (4)*
H9B	−0.462 (2)	0.0468 (14)	0.4033 (12)	0.017 (3)*
H9C	−0.333 (2)	0.1296 (15)	0.3011 (13)	0.022 (4)*
C10	0.25748 (16)	0.25979 (12)	0.21977 (10)	0.0166 (2)
H10	0.239 (2)	0.2061 (14)	0.1678 (12)	0.017 (3)*
C11	0.40602 (16)	0.32201 (12)	0.17634 (9)	0.0157 (2)
C12	0.53935 (16)	0.28850 (12)	0.06331 (9)	0.0160 (2)
C13	0.68703 (17)	0.43854 (12)	0.12030 (10)	0.0177 (2)
C14	0.85791 (16)	0.32219 (12)	−0.05548 (10)	0.0166 (2)
H14A	0.922 (2)	0.4040 (16)	−0.0822 (13)	0.024 (4)*
H14B	0.819 (2)	0.3053 (15)	−0.1204 (13)	0.020 (3)*
C15	1.00626 (16)	0.18907 (12)	−0.01512 (9)	0.0162 (2)
C16	1.19038 (18)	0.14177 (14)	−0.10274 (11)	0.0206 (2)
H16A	1.154 (2)	0.1391 (18)	−0.1711 (15)	0.037 (4)*
H16B	1.270 (2)	0.0529 (17)	−0.0750 (14)	0.025 (4)*
H16C	1.254 (3)	0.2144 (19)	−0.1146 (16)	0.045 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01803 (16)	0.02014 (16)	0.01488 (15)	−0.00891 (11)	0.00277 (11)	−0.00591 (11)
O1	0.0189 (4)	0.0252 (4)	0.0137 (4)	−0.0090 (3)	−0.0002 (3)	−0.0052 (3)
O2	0.0161 (4)	0.0196 (4)	0.0167 (4)	−0.0048 (3)	0.0070 (3)	−0.0055 (3)
O3	0.0143 (4)	0.0281 (4)	0.0190 (4)	−0.0113 (3)	0.0031 (3)	−0.0072 (3)
O4	0.0235 (4)	0.0344 (5)	0.0172 (4)	−0.0160 (4)	0.0027 (3)	−0.0105 (3)
O5	0.0280 (5)	0.0328 (5)	0.0228 (4)	−0.0206 (4)	0.0054 (4)	−0.0099 (4)
O6	0.0254 (5)	0.0255 (4)	0.0154 (4)	−0.0080 (4)	−0.0023 (3)	−0.0022 (3)
N1	0.0134 (4)	0.0203 (5)	0.0133 (4)	−0.0073 (4)	0.0027 (3)	−0.0039 (3)
C1	0.0135 (5)	0.0184 (5)	0.0136 (5)	−0.0058 (4)	0.0004 (4)	−0.0014 (4)
C2	0.0136 (5)	0.0196 (5)	0.0154 (5)	−0.0065 (4)	−0.0009 (4)	−0.0024 (4)
C3	0.0148 (5)	0.0150 (5)	0.0139 (5)	−0.0029 (4)	−0.0017 (4)	−0.0028 (4)
C4	0.0133 (5)	0.0151 (5)	0.0143 (5)	−0.0033 (4)	0.0031 (4)	−0.0027 (4)
C5	0.0114 (5)	0.0169 (5)	0.0181 (5)	−0.0052 (4)	−0.0001 (4)	−0.0016 (4)
C6	0.0141 (5)	0.0194 (5)	0.0144 (5)	−0.0061 (4)	−0.0003 (4)	−0.0031 (4)
C7	0.0210 (6)	0.0246 (6)	0.0170 (5)	−0.0091 (5)	−0.0039 (4)	−0.0045 (4)
C8	0.0253 (6)	0.0266 (6)	0.0151 (5)	−0.0088 (5)	0.0036 (5)	−0.0021 (5)
C9	0.0193 (6)	0.0239 (6)	0.0206 (6)	−0.0111 (5)	−0.0029 (4)	−0.0039 (5)
C10	0.0146 (5)	0.0215 (5)	0.0140 (5)	−0.0062 (4)	−0.0009 (4)	−0.0034 (4)
C11	0.0142 (5)	0.0190 (5)	0.0136 (5)	−0.0047 (4)	−0.0010 (4)	−0.0034 (4)
C12	0.0134 (5)	0.0205 (5)	0.0142 (5)	−0.0067 (4)	−0.0009 (4)	−0.0017 (4)
C13	0.0178 (5)	0.0192 (5)	0.0165 (5)	−0.0080 (4)	−0.0001 (4)	−0.0028 (4)
C14	0.0138 (5)	0.0207 (5)	0.0143 (5)	−0.0072 (4)	0.0025 (4)	−0.0029 (4)
C15	0.0167 (5)	0.0197 (5)	0.0158 (5)	−0.0092 (4)	−0.0021 (4)	−0.0051 (4)
C16	0.0162 (5)	0.0231 (6)	0.0217 (6)	−0.0063 (5)	0.0005 (4)	−0.0049 (5)

Geometric parameters (Å, º)

S1—C11	1.7567 (11)	C5—C6	1.3874 (15)
S1—C13	1.7747 (12)	C6—H6	0.942 (14)
O1—C3	1.3629 (13)	C7—H7A	0.971 (15)
O1—C7	1.4405 (14)	C7—H7B	0.979 (15)
O2—C4	1.3762 (13)	C7—H7C	0.994 (15)
O2—C8	1.4320 (15)	C8—H8A	0.969 (16)
O3—C5	1.3714 (13)	C8—H8B	0.988 (15)
O3—C9	1.4312 (14)	C8—H8C	0.977 (17)
O4—C12	1.2134 (14)	C9—H9A	0.980 (15)
O5—C13	1.2067 (14)	C9—H9B	0.966 (14)
O6—C15	1.2191 (14)	C9—H9C	1.001 (14)
N1—C13	1.3851 (14)	C10—C11	1.3466 (15)
N1—C12	1.3900 (14)	C10—H10	0.948 (14)
N1—C14	1.4529 (14)	C11—C12	1.4845 (15)
C1—C6	1.4009 (14)	C14—C15	1.5231 (16)
C1—C2	1.4012 (15)	C14—H14A	1.016 (15)
C1—C10	1.4590 (15)	C14—H14B	0.947 (14)
C2—C3	1.3901 (15)	C15—C16	1.4941 (16)
C2—H2	0.946 (16)	C16—H16A	0.926 (17)
C3—C4	1.4094 (15)	C16—H16B	0.951 (16)
C4—C5	1.3996 (15)	C16—H16C	0.937 (19)
C11—S1—C13	91.48 (5)	H8A—C8—H8C	111.8 (13)
C3—O1—C7	116.50 (9)	H8B—C8—H8C	112.4 (13)
C4—O2—C8	114.25 (8)	O3—C9—H9A	110.0 (8)
C5—O3—C9	115.87 (9)	O3—C9—H9B	106.0 (8)
C13—N1—C12	116.31 (9)	H9A—C9—H9B	111.2 (12)
C13—N1—C14	120.69 (9)	O3—C9—H9C	110.8 (8)
C12—N1—C14	121.22 (9)	H9A—C9—H9C	110.3 (12)
C6—C1—C2	120.03 (10)	H9B—C9—H9C	108.4 (11)
C6—C1—C10	116.52 (9)	C11—C10—C1	130.61 (10)
C2—C1—C10	123.37 (10)	C11—C10—H10	114.0 (9)
C3—C2—C1	119.64 (10)	C1—C10—H10	115.4 (9)
C3—C2—H2	120.0 (9)	C10—C11—C12	119.86 (10)
C1—C2—H2	120.3 (9)	C10—C11—S1	129.49 (9)
O1—C3—C2	124.35 (10)	C12—C11—S1	110.60 (8)
O1—C3—C4	115.33 (9)	O4—C12—N1	123.07 (10)
C2—C3—C4	120.32 (10)	O4—C12—C11	126.41 (10)
O2—C4—C5	120.89 (10)	N1—C12—C11	110.51 (9)
O2—C4—C3	119.44 (9)	O5—C13—N1	124.82 (11)
C5—C4—C3	119.61 (10)	O5—C13—S1	124.25 (9)
O3—C5—C6	123.72 (10)	N1—C13—S1	110.93 (8)
O3—C5—C4	116.29 (10)	N1—C14—C15	111.00 (9)
C6—C5—C4	119.99 (10)	N1—C14—H14A	110.1 (8)
C5—C6—C1	120.34 (10)	C15—C14—H14A	109.8 (8)
C5—C6—H6	120.6 (9)	N1—C14—H14B	109.6 (9)
C1—C6—H6	119.1 (9)	C15—C14—H14B	108.5 (9)
O1—C7—H7A	105.8 (9)	H14A—C14—H14B	107.8 (12)
O1—C7—H7B	108.4 (9)	O6—C15—C16	123.34 (11)
H7A—C7—H7B	109.4 (12)	O6—C15—C14	120.60 (10)
O1—C7—H7C	109.2 (8)	C16—C15—C14	116.04 (10)
H7A—C7—H7C	111.3 (12)	C15—C16—H16A	107.2 (10)
H7B—C7—H7C	112.5 (12)	C15—C16—H16B	111.7 (10)
O2—C8—H8A	108.7 (9)	H16A—C16—H16B	112.3 (14)
O2—C8—H8B	107.5 (9)	C15—C16—H16C	104.2 (11)
H8A—C8—H8B	106.5 (13)	H16A—C16—H16C	109.2 (15)
O2—C8—H8C	109.8 (10)	H16B—C16—H16C	111.7 (14)
C6—C1—C2—C3	−1.73 (17)	C2—C1—C10—C11	−15.5 (2)
C10—C1—C2—C3	−178.19 (10)	C1—C10—C11—C12	172.00 (11)
C7—O1—C3—C2	−1.74 (15)	C1—C10—C11—S1	−5.3 (2)
C7—O1—C3—C4	177.64 (10)	C13—S1—C11—C10	175.08 (11)
C1—C2—C3—O1	178.73 (10)	C13—S1—C11—C12	−2.42 (8)
C1—C2—C3—C4	−0.62 (17)	C13—N1—C12—O4	−176.61 (11)
C8—O2—C4—C5	82.74 (13)	C14—N1—C12—O4	−11.70 (17)
C8—O2—C4—C3	−100.09 (12)	C13—N1—C12—C11	2.50 (14)
O1—C3—C4—O2	6.01 (15)	C14—N1—C12—C11	167.41 (9)
C2—C3—C4—O2	−174.59 (9)	C10—C11—C12—O4	1.81 (18)
O1—C3—C4—C5	−176.78 (10)	S1—C11—C12—O4	179.59 (10)
C2—C3—C4—C5	2.62 (16)	C10—C11—C12—N1	−177.26 (10)
C9—O3—C5—C6	16.49 (16)	S1—C11—C12—N1	0.52 (12)
C9—O3—C5—C4	−163.65 (10)	C12—N1—C13—O5	176.35 (11)
O2—C4—C5—O3	−4.97 (15)	C14—N1—C13—O5	11.36 (18)
C3—C4—C5—O3	177.86 (10)	C12—N1—C13—S1	−4.36 (13)
O2—C4—C5—C6	174.89 (10)	C14—N1—C13—S1	−169.35 (8)
C3—C4—C5—C6	−2.27 (16)	C11—S1—C13—O5	−176.90 (11)
O3—C5—C6—C1	179.79 (10)	C11—S1—C13—N1	3.80 (9)
C4—C5—C6—C1	−0.06 (17)	C13—N1—C14—C15	85.05 (12)
C2—C1—C6—C5	2.08 (17)	C12—N1—C14—C15	−79.20 (12)
C10—C1—C6—C5	178.78 (10)	N1—C14—C15—O6	−0.64 (14)
C6—C1—C10—C11	167.88 (12)	N1—C14—C15—C16	−179.20 (9)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C1–C6 and S1/N1/C11–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O6^i	0.942 (14)	2.398 (14)	3.3108 (14)	163.2 (12)
C7—H7A···O5^ii	0.971 (15)	2.482 (15)	3.4434 (15)	170.4 (13)
C14—H14A···O5^iii	1.016 (15)	2.335 (15)	3.2659 (14)	151.8 (11)
C7—H7C···Cg1^iv	0.994 (15)	2.755 (15)	3.5131 (14)	133.3 (11)
C9—H9C···Cg2^i	1.001 (14)	2.900 (15)	3.8441 (14)	157.5 (11)

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z; (iv) −x, −y+1, −z+1.